How to Dress Upscale Casual in 5 Easy Steps

5 Easy Steps to Upscale Casual

You’ve got your workweek down pat.  Monday through Friday, you know what you’re doing, and you know what you’re wearing (at least most days).  But come Saturday morning, you want to look great and still feel comfortable. You want to go Upscale Casual. Many clients have told me over the years that they have no idea what to wear.  Sadly, they default to their frumpy side and pull on those jeans that they’ve had for ten years or more, pair with a baggy, ill-fitting top and shoes that bring the entire look down.

It’s the weekend

One issue I see so many clients dealing with is bridging the gap between looking professional and looking casual. Often, after coming home from work (looking polished and pulled together) they slip into sloppy sweatpants and a nondescript tee shirt that is devoid of shape. They go from all to nothing in the blink of an eye, when it comes to style, and don’t even look like the same person. Just hope no one drops by to say hello!

While I am a big believer in having your favorite comfy clothes to lounge around the house when you know no one will see you, I’d like to encourage you to build a wardrobe that has plenty of casual options that you’ll feel great about being seen in! It can be done. I want to show you just how quickly you can have a wardrobe that goes from dressy to casual without missing a beat.

What is Upscale Casual?

First, let’s redefine casual. I like to think of casual clothes like jeans and a t-shirt, perhaps a pair of sneakers and little else. Casual to me is what you wear around the house or to work in the yard. I realize that it’s my nature to be a little overdressed but what I’ve found is that when women are dressed casually for an event, they typically feel underdressed, and not quite as confident as they’d like. So let’s talk about one of my favorite forms of dress, which is what I refer to as Upscale Casual. 

Now upscale casual is an excellent form of dress for women that can be appropriate for both the workplace and the weekends, and leave you feeling as if you can get more done during the day because you don’t have to stop and change your whole look. The beauty of upscale casual is there are a few small, but essential details that make this look what it is. Read: it’s simple! However, like any great wardrobe, it just takes a little planning. Let me take you through the process, and you’ll see what I mean!

1/ First, start with a great pair of pants

Find a pair of pants that feel great, fit you to a tee and are versatile.  Our modern fit pants are perfect, giving you both comfort and style.  But jeans work well here too!  The right pair of jeans that is.  Forget that faded pair of ‘mom’ jeans you’ve had for a few years. You want your jeans to look fresh and modern and be the best fit you can find. This is key because the wrong kind of jeans (baggy, ill-fitting) will ruin in the look.

2/ Next you want to choose the right top

Start with a solid knit top in one of your best colors. Skip the beefy tees and opt for something more feminine that shows your shape. If you’re feeling bold and want to wear a print or texture, you’ll get a bit more of a boost. Simple works just as well here. That’s the beauty of this look! Try a Tees by Tina top, a tunic or a lightweight sweater.

3/ Now it’s time for my favorite item, the third layer

Add in a chic cardigan, a liquid leather jacket, a vest or even a wrap, and it elevates your look to something fabulous!  The third layer is what makes this look to the next level and creates a look that is greater than the sum of its parts. It’s magical!

4/ If the Shoe Fits

If you’re puttering around the house, all you need are a cute pair of athletically inspired flats (skip the big sneakers). If you’re heading to the office or out for dinner swap your flats for chic boots or booties (skip the clunky black shoes), add in some fun jewelry and a great scarf that enhances your eye color. This will dresses up your look and take it to an entirely new level! The accessories are the icing on the cake. Change them out and you can transform the look from simple to more dressy.

5/ Hair and Makeup

To add polish to your look and feel more put together, hair and makeup are what you should always have in place if you’re heading to work, but even on the weekends, you want to opt for a casually elegant style that helps you feel great while still looking like you didn’t do a thing! Master the art of the chic ponytail or the wash and go style for weekend chic. Keep your makeup simple and do the basics–lips, mascara, and brows–and you’ll look polished without looking like you tried too hard.

While the beauty of the upscale casual look lies in its simplicity, feel free to put your spin on it! If you want to elaborately layer a couple of tops and a funky jacket that’s just your style, go for it! Add in a great pair of heels or if flats are more your style, find a chic yet comfortable pair that makes you feel great! This look is open to interpretation, so find the strategy that makes you feel fabulous while helping you to get dressed with ease!


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